156:  Lessons from Losing a Million Dollars with Joshua Wilson

The Modern Man Podcast

156: Lessons from Losing a Million Dollars with Joshua Wilson

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Published on May 23, 2025, 9:00:00 AM
Total time: 00:49:26

Episode Description

In this episode of the Modern Man Podcast, host Ted speaks with Joshua Wilson, a serial entrepreneur and business acquisition strategist. They discuss Joshua's journey from being a real estate addict to successfully acquiring and transforming businesses


Takeaways

  • Joshua Wilson transitioned from real estate to mergers and acquisitions.
  • Being equity-rich but cash-poor can be a challenging situation.
  • Diversification is crucial for financial stability.
  • Taking calculated risks can lead to significant rewards.
  • Mental roadblocks often prevent individuals from pursuing opportunities.
  • Due diligence is essential when acquiring a business.
  • Identifying growth potential in businesses is key to successful acquisitions.
  • Entrepreneurship requires resilience and the ability to learn from failures.
  • Networking and mentorship can provide valuable insights and opportunities.
  • The universe often presents opportunities when you are open to receiving them. Don't do restaurants, just too low margins.
  • Niche down as much as you can.
  • Immediate cash flow from acquisitions is a key advantage.
  • Aligning with investors is crucial for success.
  • There is no such thing as a passive business.
  • Creating multiple income streams is essential for financial freedom.
  • Diversification is necessary to avoid being cash poor.
  • Investing in businesses can yield better returns than real estate.
  • Understanding the operational side of business is vital for success.
  • Parenthood has shaped my perspective on financial independence.



Chapters

00:18 - Introduction to the Modern Man Podcast

01:38 - From Real Estate to Mergers and Acquisitions

03:21 - Understanding Equity Rich and Cash Poor

06:20 - The Importance of Diversification in Business

09:08 - Taking Calculated Risks in Entrepreneurship

12:22 - The Journey of an Entrepreneur: Lessons Learned

15:16 - Overcoming Mental Roadblocks and Fear

18:28 - The Role of Due Diligence in Business Acquisition

21:23 - Identifying Profitable Business Opportunities

24:05 - Niche Down for Success

27:18 - Immediate Cash Flow from Acquisitions

30:25 - Investing with Limited Cash

33:31 - The Reality of Business Ownership

38:58 - Creating Multiple Income Streams

40:52 - Long-Term Vision in M&A

42:45 - Life Lessons from Parenthood


Wilson’s Links

Website: https://jwenterprise.co/

Instagram: https://www.instagram.com/therealjoshwilson

Facebook: https://www.facebook.com/realjwilson/


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More about The Modern Man Podcast

“The Modern Man” is a series focused on discussing the challenges and obstacles men face in today’s society. It is an open forum of discussion where thoughts, strategies and ideas of men living a happy and fulfilled life are explored. The Modern Man aims to create a community of men not only sharing and connecting on a deeper level, but also exploring how to thrive and live a happy and fulfilled life. This is done through intentional conversations strategically aimed at issues that men face in today’s society.